Abstract
An efficient procedure has been developed for the synthesis of 1H-indazolo[2,1-b]phthalazine-triones by the one-pot condensation of cyclohexane-1,3-dione, aromatic aldehydes and phthalhydrazides catalysed by proline triflate under solvent-free conditions. The reaction proceeds in good to excellent yields.
Keywords
References
1.
Ramón D.J.
, and
Yus M.
, Angew. Chem. Int. Ed. , 1997 , 44 , 1602 .
2.
Razaeli F.
,
Hamid A.
, and
Nahid F.
, Open Catal. J. , 2010 , 3 , 14 .
3.
Orru R.V.A.
, and
Greef M.D.
, Synthesis , 2003 , 10 , 1471 .
4.
Kidwai M.
,
Venkataramamam R.
,
Mohan R.
, and
Sapra P.
, Curr. Med. Chem. , 2002 , 9 , 1209 .
5.
Ugi I.
,
Domling A.
, and
Werner B.
, J. Heterocyclic Chem. , 2000 , 36 , 274 .
6.
Corbett J.W.
, Org. Prep. Proced. Int. , 2009 , 30 , 489 .
7.
Chauhan P.M.S.
, and
Srivastava S.K.
, Comb. Chem. High T. Scr. , 2001 , 4 , 35 .
8.
Terrett N.K.
,
Bell A.S.
,
Brown D.
, and
Ellis P.
, Bioorg. Med. Chem. Lett. , 1996 , 6 , 1819 .
9.
Genin M.J.
,
Biles C.
,
Keiser B.J.
,
Poppe S.M.
,
Swaney S.M.
,
Tarpley W.G.
,
Yagi Y.
, and
Romero D.L.
, J. Med. Chem. , 2000 , 43 , 1034 .
10.
Hagiwara M.
,
Endo T.
,
Kanayama T.
, and
Hidaka H.
, J. Pharmacol. Exp. Ther. , 1984 , 228 , 467 .
11.
Grasso S.
,
DeSarro G.
,
Micale N.
,
Zappala M.
,
Puia G.
,
Baraldi M.
, and
Demicheli C.
, J. Med. Chem. , 2000 , 43 , 2851 .
12.
Domling A.
, and
Ugi I.
, Angew. Chem. Int. Ed. , 2000 , 39 , 3168 .
13.
Nomoto Y.
,
Obase H.
,
Takai H.
,
Teranishi M.
,
Nakamura J.
, and
Kubo K.
, Chem. Pharm. Bull. , 1990 , 38 , 2179 .
14.
Heine H.W.
,
Baclawski L.M.
,
Bonser S.M.
, and
Wachob G.D.
, J. Org. Chem. , 1976 , 41 , 3229 .
15.
Sheradsky T.
, and
Moshenberg R.
, J. Org. Chem. , 1986 , 51 , 3123 .
16.
Sayyafi M.
,
Seyyedhamzeh M.
,
Khavasi H.R.
, and
Bazgir A.
, Tetrahedron , 2008 , 64 , 2375 .
17.
Liu L.P.
,
Lu J.M.
, and
Shi M.
, Org. Lett. , 2007 , 9 , 1303 .
18.
Sayyafi M.
,
Seyyedhamzed M.
,
Khavasi H.R.
, and
Bazgir A.
, Tetrahedron , 2008 , 64 , 2375 .
19.
Funatomi T.
,
Wakasugi K.
,
Misaki T.
, and
Tanabe Y.
, Green Chem. , 2006 , 8 , 1022 .
20.
Wakasugi K.
,
Misaki T.
,
Yamada K.
, and
Tanabe Y.
, Tetrahedron Lett. , 2000 , 41 , 5249 .
21.
Li J.J.
,
Li J.
, and
Su W.K.
, J. Chem. Res. , 2009 , 499 .
22.
Sabitha G.
,
Srinivas C.
,
Raghavendar A.
, and
Yadav J.S.
, Helv. Chim. Acta , 2010 , 93 , 1375 .
23.
Fazaeli R.
,
Aliyan H.
, and
Fazaeli N.
, J. Heterocyclic Chem. , 2009 , 46 , 728 .
24.
Khurana J.M.
, and
Magoo D.
, Tetrahedron Lett. , 2009 , 50 , 7300 .
25.
Ghorbani-Vaghei R.
,
Karimi-Nami R.
,
Toghraei-Semiromi Z.
,
Amiri M.
, and
Ghavidel M.
, Tetrahedron , 2011 , 67 , 1930 .
26.
Li J.J.
,
Lu L.M.
, and
Su W.K.
, Tetrahedron Lett. , 2010 , 51 , 2434 .